Sodium Bicarbonate → HCID 121268, compound

HRID 1366115Notes

Reaction equation

HRID 1366115 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH3:2].C([O-])(O)=O.[Na+]>C1CCCCC=1.CCO.CO.O.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([S:7]([NH:6][CH2:5][CH2:4][N:3]([CH2:19][CH3:20])[CH2:1][CH3:2])(=[O:8])=[O:9])=[CH:11][CH:12]=1

Participants

8

Reactant 2

HCID 516892Sodium BicarbonateHCID 4572956HCID 4572956, compound

Product 1

HCID 121268HCID 121268, compound

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8079CyclohexeneSolvent

Procedure

A mixture of N-(2-diethylaminoethyl)-4-nitrobenzenesulfonamide (0.72 g, 2.13 mmol) in cyclohexene (4.8 mL) and EtOH (24 mL) is heated using an oil bath until dissolution had almost been achieved. At this point Pd on C (144 mg, 10% (w/w)) is added, and the mixture heated at reflux for 5 hours. After this time the solution is cooled to room temperature, then filtered through Hy-flo. The filtrate is evaporated in vacuo to afford a yellow gum. The yellow gum is dissolved in the minimum quantity of methanol, then NaHCO3 (1 eq.) dissolved in water, is added. The mixture is stirred at room temperature, then the mixture extracted with EtOAc (2×). The combined organic layers are dried (MgSO4), and evaporated to afford the title aniline.

Workup

  1. temperatureis heated
  2. dissolutionuntil dissolution
  3. temperaturethe mixture heated
  4. temperatureat reflux for 5 hours
  5. filtrationfiltered through Hy-flo
  6. customThe filtrate is evaporated in vacuo
  7. customto afford a yellow gum
  8. additionis added
  9. extractionthe mixture extracted with EtOAc (2×)
  10. dry with materialThe combined organic layers are dried (MgSO4)
  11. customevaporated

Sources & evidence

ORD record
ord-2e109ccacb7d46219a7ae44455737db6
Source dataset
uspto-grants-2011_02
Patent number
US07893058B2

Reaction notes

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